Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions

Brinkmann, Yasmin; Madhushaw, Reniguntala Johnson; Jazzar, Rodolphe; Bernardinelli, Gérald Hugues; Kundig, Ernst Peter

doi:10.1016/j.tet.2007.06.033

Scientific article

English

Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions

Contributors

Brinkmann, Yasmin; Madhushaw, Reniguntala Johnson; Jazzar, Rodolphe; Bernardinelli, Gérald Hugues; Kundig, Ernst Peter

Published in

Tetrahedron, vol. 63, no. 35, p. 8413-8419

Publication date

2007

Abstract

The synthesis of the chiral ligand (R,R)-BIPHOP-F is detailed. Its coordination to a cationic cyclopentadienyl ruthenium fragment generates [Ru (acetone)(R,R)-BIPHOP-F)Cp][SbF6], a transition metal Lewis acid that catalyzes the [3+2] dipolar cycloaddition reaction between aryl nitrile oxides and α,β-unsaturated aldehydes to give chiral 2-isoxazolines with yields of 43–98% and asymmetric purity of 60–93% ee. The stereochemistry of the major enantiomer is S, consistent with an approach of the nitrile oxide to the Cα-Si face of the enal in the anti-s-trans conformation in the catalyst site.

UNIGE affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

BRINKMANN, Yasmin et al. Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions. In: Tetrahedron, 2007, vol. 63, n° 35, p. 8413–8419. doi: 10.1016/j.tet.2007.06.033

Article

Identifiers

PID : unige:7057
DOI : 10.1016/j.tet.2007.06.033

Journal ISSN

0040-4020

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Chiral ruthenium Lewis acid-catalyzed nitrile oxide cycloadditions

Contributors

Published in

Publication date

Abstract

UNIGE affiliation entities

Citation (ISO format)

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Journal ISSN

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Creation

First validation

Update

Status update

Last indexation